Just a note to you crazy guys and gals - any hotel around Midway airport in Chicago is the same distance, if not farther, away from downtown Chicago than the Itasca hotel. Also, the area around Midway isn't the greatest.

If you were to have it in Chicago, I suggest actually staying in a downtown hotel. Then you can really walk around, shop and do touristy things. There are also hotels in the North side of Chicago, which is close to downtown and in a nicer location with lots little shops and restaurants.